Microsoft Windows Server 2012 R2 in place upgrade to 2016 2019 notes for reference Keep Personal Files Grayed out

For those fighting with in place upgrades not working and keeping your files, here are some suggestions that I just realized and forgot from my 2019 and 2020 experiences upgrading 2008 and 2012 R2 servers to 2016 and 2019 respectively for medical offices needing their ChiroTouch client/server upgrades to continue.

after copying the ISO files to a folder I ran the following:

dism /mount-wim /wimfile:c:\ISO\sources\install.wim /mountdir:c:\mount /index:2

dism /image:c:\mount /get-currentedition

dism /image:c:\mount /get-targeteditions

dism /image:c:\mount /set-edition:ServerStandard

dism /unmount-wim /mountdir:c:\mount /commit

Then I ran the setup file and it still listed eval under the options, but then it allowed me to choose to keep my files.

alas, after mounting the image, my version of DISM 6.3.9 would not perform the following commands, so I downloaded the latest ADK and installed it on the server with the default values. The dism command still failed, unless I pointed the DISM command to the latest 10.x path in the install folder. then the rest of the commands completed, and installation of the Windows Server 2016/2019 would allow me to keep my files and applications.

REF 1: https://www.microsoft.com/en-us/evalcenter/download-windows-server-2019

REF 2: https://www.microsoft.com/en-us/evalcenter/download-windows-server-2016

REF 3: https://answers.microsoft.com/en-us/windowserver/forum/all/keep-personal-files-and-apps-option-greyed-out/15b6fd41-6cce-4769-8fc0-b42c7f4c65f3

REF 4: https://learn.microsoft.com/en-us/windows-hardware/get-started/adk-install

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